Last year, about this time, my boss IM’d me and my counterpart, her other direct report. “Can you both please call into my conference bridge?”

I dialed in first, and as we were momentarily the only ones on the bridge, she began. “Dan. I’ve been offered another position at another company, and I’m going to take it.”

I didn’t hesitate. There was only one thing to say.

“Can I go, too?”

She laughed. In retrospect, I probably came off a bit desperate.

Later that day, I thought about that conversation. When I first joined that particular company, I interviewed with no less than 6 different people. By the time the interview process finished, I was wondering if there was anyone in the company I hadn’t met. It had been 18 months, and I realized that she was the last of those original 6 still at the company. That had to mean something, and every way I looked at it, it wasn’t a good indicator.

When it’s time to move on from something in life, you just know. Plenty of people know how to ignore that feeling, but I’m not one of them. Sometimes, when you’re thinking things are secure – BAM! – something happens. Your boss leaves. Your pay structure changes. Your team gets shifted to another department. You wonder if security is an illusion.

Security IS an illusion.

It doesn’t matter who you are. A CEO, making $50 million dollars a year still has to worry every day that the shareholders may call for their resignation if growth doesn’t meet the expected projections. A maintenance worker still has to worry that their position does not become outsourced to a 3rd party company, hiring contractors willing to do the same job for less money and no health benefits.

What perpetuates the a fore mentioned security illusion is that antiquated ideal of the “American Dream”. Get a “stable” job. Get a house with a 30 year mortgage. By the time you are ready to retire, the house will be paid off and you can live out the rest of your days in peace. It sounds so great in theory and looks even better on paper, but if your job situation changes, or the economy changes, and you can’t make that mortgage payment – then what?

My plan is different. My plan is a rollercoaster; you will ride it when you could be with your friends, because of the rush it gives; the highs and the lows. You’ll be supported by the “stability” of the job you already have, and you’ll use that stability for whatever it is worth.

Here are the steps you have to take:

1. Start thinking about what you know more about than MOST people. It could be beer. It could be art. It could be comics. It could be real estate. It could be working out. It could be computers. It could be cooking. It could be Instagram. It could be The Hunger Games. It could be fishing. It could be Photoshop. It could be snowboarding. It could be anything.

2. Start thinking about how you can teach people who don’t know about your topic, but want to learn. People often try things one time then give up because they weren’t good at it. I hear people say all the time, “I tried but I wasn’t that good so I got frustrated and gave up.” If you look, you could find tons of skiis, rollerblades, art supplies, and much more in people’s closets. Our expectation is always to be amazing at something the first time we try it, but it doesn’t work that way. Your goal is to help those people realize that with your coaching and their hard work, they could learn enough to enjoy it.

3. IGNORE the voices that tell you “someone has already done this!” and “You don’t know enough!” Those voices are useless. You’ll come up with reasons why you shouldn’t go down this road. Tons of them. Your brain will invent new ones after your conquered the old ones. I can’t shut off my brain from coming up with more. I get angry about that and then my wife tells me “you need to change your attitude or go back to bed.”

Get used to having these voices and ignoring them.

4. Start teaching what you know. Give it away for free to your earliest learners. That’s OK, because you’re living off the money from your current job; remember the “security”?
This is your chance to hone your craft. You have to find the best way to teach people. Is it a YouTube channel? Is it an in-person class? Is it a Google Hangout session? Is it one-on-one coaching?
If you can connect with people, make them feel truly important and valuable, then it doesn’t matter if you’re teaching them in a group or one at a time.

5. Keep teaching. Start charging just a little. Some of the earliest learners who were receiving it for free will drop off. This is not rejection, it’s OK. Some people always just want things for free.
I’m can relate to those people, so I know. But I do pay for things that are valuable to me, and especially if I feel that the person I’m paying is personally invested in seeing me succeed.
If they’ve seen my struggle, know where I’m stuck, and want to help me move past that, then I’m going to happily pay them for that help; but it has to be personal.

6. Keep teaching. Start charging a bit more, and figure better ways to express the value you’re offering. More of those earliest learners will drop off. This is not rejection, it’s OK. They will be replaced by new people who want to learn what you’re teaching and because you’ve helped a number of people by this point, and the newbies have heard such good things, they’ll view you as an expert.

7. Charge more. You’ve been doing this long enough that you can command a higher rate, and you deserve it. For the people I’ve worked with so far, one common problem I see across the board is them not charging enough. They don’t feel confident enough to consider themselves as the best at what they do, so they feel uncomfortable asking higher prices. Throughout our lives, we constantly see examples of people charging different rates for the same thing, but when it comes to our work, we have the tendency to devalue ourselves. People are willing to pay more for an Mac then a PC, even though they’re both computers that do the same thing. Why is that? It’s simple. They identify with Apple’s mindset, “Think Different”. People buy from people who believe what they believe. By this point, you’ll have a dedicated group of people who have followed you because they like what you believe, and hang on your every word. As a result of all the hard work you put in with the earlier steps, you’ll never have to sell them on why they should pay more to work with you. They’ll already have seen the value you provide multiple times over.


8. Offer to teach people how to make money teaching others about THEIR topic.
This is when it gets crazy.
People will approach you and ask you for help with their own topic. You’ll know what works and what doesn’t. You’ll charge them to teach them what you know about marketing and getting clients, even if you know nothing about their topic. It’ll be completely different from what you’ve done before, yet familiar at the same time.

It’s not a plan that will be effortless. It’s a plan that requires prioritization. It’s not a plan that will reach completion within a week.

When you need a guide, I am here.


Next Tuesday (10/28) at 8PM, I’ll be hosting an online session where I build a customized plan for a client. Sign up for here for free ideas, motivation, and to see how I work.